Hydrazine hydrate (1:1) → HCID 86649765, compound

HRID 1880249Notes

Reaction equation

HRID 1880249 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12]2([C:36]([F:39])([F:38])[F:37])[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][N:24]4C(=O)C5=CC=CC=C5C4=O)=[C:19]([Cl:35])[CH:18]=3)[CH2:13]2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.O.NN>C(O)C>[NH2:24][CH2:23][C:20]1[CH:21]=[CH:22][C:17]([C:14]2[CH2:13][C:12]([C:4]3[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=[C:2]([Br:1])[CH:3]=3)([C:36]([F:37])([F:38])[F:39])[O:16][N:15]=2)=[CH:18][C:19]=1[Cl:35]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86761701HCID 86761701, compound

Product 1

HCID 86649765HCID 86649765, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5.26 g of N-[[4-[5-[3-bromo-5-(trifluoromethyl)phenyl]-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-chlorophenyl]methyl]phthalimide in 20 mL of ethanol, 0.73 g of a hydrazine monohydrate aqueous solution was added and the resultant mixture was stirred while heating the mixture to reflux for 1 hour. After the completion of the reaction, the reaction mixture was left to be cooled down to room temperature and from the reaction mixture, an insoluble substance was filtered off and the solvent was distilled off under reduced pressure. To the resultant residue, 20 mL of chloroform was added to dissolve the residue and an insoluble substance was filtered off one more time. The resultant filtrate was washed with water (10 mL×1) and then dehydrated and dried over saturated saline and anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with methanol-ethyl acetate (1:9) to obtain 2.87 g of the objective substance as a yellow resinoid.

Workup

  1. temperaturewhile heating the mixture
  2. temperatureto reflux for 1 hour
  3. customAfter the completion of the reaction
  4. waitthe reaction mixture was left
  5. filtrationan insoluble substance was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. additionTo the resultant residue, 20 mL of chloroform was added
  8. dissolutionto dissolve the residue
  9. filtrationan insoluble substance was filtered off one more time
  10. washThe resultant filtrate was washed with water (10 mL×1)
  11. dry with materialdried over saturated saline and anhydrous sodium sulfate in this order
  12. distillationthe solvent was distilled off under reduced pressure
  13. customThe resultant residue was purified by silica gel column chromatography
  14. washeluting with methanol-ethyl acetate (1:9)
  15. customto obtain 2.87 g of the objective substance as a yellow resinoid

Sources & evidence

ORD record
ord-40964b5ca7874f78bd534be5165c430a
Source dataset
uspto-grants-2012_11
Patent number
US08318757B2

Reaction notes

Loading…